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Compare 78 Cottages in Chester with updated reviews, rates, and availability.

Putnam Valley Vacation Rental: Patio & Lake Views!
Putnam Valley Vacation Rental | 3BR | 2BA | 7 Steps Required to Enter
Putnam Valley Vacation Rental: Patio & Lake Views!
9.8 out of 10, Exceptional, (11)
"Cozy, clean property. We had everything we needed for a 3-night stay for West Point Family Weekend. Several stores & restaurants conveniently nearby. Host Neury was most accommodating. Incredible views & scenery!!"
Putnam Valley Vacation Rental: Patio & Lake Views!
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is SAR 631
SAR 935 total
includes taxes & fees
30 Nov - 1 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Home Sweet Home ...
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Quaint village, walk to restaurants and shops.
Exterior detail
Quaint village, walk to restaurants and shops.
9.8 out of 10, Exceptional, (9)
"Wonderfully quaint place within walking distance of downtown restaurants/pubs. Cant wait to come back"
Quaint village, walk to restaurants and shops.
Historic Cornwall-On-Hudson Cottage w/ Deck!
Cornwall-On-Hudson Vacation Rental | 2BR | 2BA | Stairs Required | 2,000 Sq Ft
Historic Cornwall-On-Hudson Cottage w/ Deck!
10.0 out of 10, Exceptional, (21)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic Cornwall-On-Hudson Cottage w/ Deck!
Putnam Valley Vacation Rental: Patio & Lake Views!
Terrace/patio
Putnam Valley Vacation Rental: Patio & Lake Views!
3.0 star property
Putnam Valley Vacation Rental: Patio & Lake Views!
Cozy Cottage Getaway, Grill, Walk to Lake
Enjoy the morning sunlight streaming through the windows while staying cozy inside. Pull down filter shades on all windows for privacy. (Use of fireplace is not allowed unfortunately!)
Cozy Cottage Getaway, Grill, Walk to Lake
10.0 out of 10, Exceptional, (14)
"My husband and I were very happy with our stay here. Sara was a communicative and flexible host, even before we arrived. The place matched our expectations from the listing. The cottage was clean, comfortable and had everything we needed for our multiple day stay. "
The price is SAR 648
SAR 1,515 total
includes taxes & fees
4 Dec - 5 Dec
Cozy Cottage Getaway, Grill, Walk to Lake
Cottage at Millpond Falls - A Romantic and Luxurious Escape
The Cottage at Millpond Falls is a romantic getaway -- an luxury experience you won't forget.
Cottage at Millpond Falls - A Romantic and Luxurious Escape
10.0 out of 10, Exceptional, (142)
"Such a beautiful location. The cottage is quant while having all the modern updates. The hosts have carefully left an array of coffee and welcome goodies, including fresh eggs from their ducks. Will be back! "
Cottage at Millpond Falls - A Romantic and Luxurious Escape
A romantic cottage and artist's retreat looking down over an enchanted lake
Stunning views
A romantic cottage and artist's retreat looking down over an enchanted lake
9.4 out of 10, Exceptional, (95)
"We cannot overstate how perfect this cottage was for us to have a quiet retreat. The place has all you need to unwind and drink in the view. The owners went above and beyond (we stayed 2 full months!). Everything was lovely, thanks Julia :)"
A romantic cottage and artist's retreat looking down over an enchanted lake
NEW Spacious 5 bedrooms with Private Lake & Beach Access and Kayak!
Living area
NEW Spacious 5 bedrooms with Private Lake & Beach Access and Kayak!
10.0 out of 10, Exceptional, (5)
"The house is even more beautiful than the photos. From the spa-like bathrooms, to toys and books for kids, to the little extra amenities like qtips and bandaids, it was the perfect getaway for everyone in our party of all ages."
NEW Spacious 5 bedrooms with Private Lake & Beach Access and Kayak!
Beautiful Cottage in Hudson Valley w/Pool & Views
Interior
Beautiful Cottage in Hudson Valley w/Pool & Views
9.8 out of 10, Exceptional, (10)
"The house was exactly as advertised. It was clean, well maintained and comfortable! The location was beautiful and private yet close to nearby stores and activities."
The price is SAR 1,126
SAR 2,621 total
includes taxes & fees
3 Dec - 4 Dec
Beautiful Cottage in Hudson Valley w/Pool & Views
Dreamy Hudson Valley Cottage w/ State Park Views
Garrison Vacation Rental | 1BR | 1BA | 650 Sq Ft | Steps Required
Dreamy Hudson Valley Cottage w/ State Park Views
9.8 out of 10, Exceptional, (11)
"Absolutely gorgeous house! Great location and a beautiful view from the porch. Would highly recommend to anyone. "
Dreamy Hudson Valley Cottage w/ State Park Views
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Private kitchen
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (8)
"Ginny was so friendly, this was beyond my expectations and would use her again."
The price is SAR 619
SAR 1,173 total
includes taxes & fees
24 Nov - 25 Nov
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Cozy Haven: A Romantic Retreat in our Tiny House!
Room
Cozy Haven: A Romantic Retreat in our Tiny House!
7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is SAR 563
SAR 1,006 total
includes taxes & fees
25 Nov - 26 Nov
Cozy Haven: A Romantic Retreat in our Tiny House!
Dreamy Hudson Valley Cottage w/ State Park Views
Living area
Dreamy Hudson Valley Cottage w/ State Park Views
3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Greenwood Lake Cottage w/ Shared Dock & Hot Tub!
Hewitt Vacation Rental | 1BR | 1BA | 350 Sq Ft | Stairs Required
Greenwood Lake Cottage w/ Shared Dock & Hot Tub!
10.0 out of 10, Exceptional, (2)
"Very clean, convenient, accessible and the host’s are Great too! Will stay again when in town"
Greenwood Lake Cottage w/ Shared Dock & Hot Tub!
Lakefront Getaway : Mountain & Lakes views
Property grounds
Lakefront Getaway : Mountain & Lakes views
10.0 out of 10, Exceptional, (4)
"The property is beautiful and relaxing, exactly what we needed. The house is cozy with full amenities needed if you were staying longer than just a few nights."
Lakefront Getaway : Mountain & Lakes views
Delightful Home w/ Fire Pit, Walk to Lake!
Living area
Delightful Home w/ Fire Pit, Walk to Lake!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very clean, easy access perfect location near my family for a birthday, silvia was very quick to respond to any questions!!"
Delightful Home w/ Fire Pit, Walk to Lake!
Hello Small Stone
Exterior
Hello Small Stone
9.6 out of 10, Exceptional, (4)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
The price is SAR 676
SAR 1,145 total
includes taxes & fees
4 Dec - 5 Dec
Hello Small Stone
Warwick Vacation Rental w/ Private Yard & Fire Pit
Living area
Warwick Vacation Rental w/ Private Yard & Fire Pit
3.0 star property
10.0 out of 10, Exceptional, (1)
"I was relieved to find that the property looks just like and even better than the pictures online. "
Warwick Vacation Rental w/ Private Yard & Fire Pit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chester

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is SAR 631
SAR 935 total
includes taxes & fees
30 Nov - 1 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Located next to the Ski Resort, Bike Park and Water Park
Swimming pool view
Located next to the Ski Resort, Bike Park and Water Park
10.0 out of 10, Exceptional, (153)
"It’s our second time staying in this condo. We love it and hope to use it again. "
Located next to the Ski Resort, Bike Park and Water Park
Beautiful Private Stone Home in the Hudson Valley
Exterior
Beautiful Private Stone Home in the Hudson Valley
10.0 out of 10, Exceptional, (138)
"home and amenities enjoyed by all age groups. the city-slickers were thrilled by the deer, and visiting the chickens and roosters. the location is beautiful and rural. easy drive from nyc and capital district."
Beautiful Private Stone Home in the Hudson Valley
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Chester cost?
Cottages in Chester range between SAR 563 and SAR 1,126 per night. These stays offer a chance to get in touch with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chester with Expedia?
Reserving a cottage in Chester is as easy as clicking on your travel dates and choosing an ideal place for a vacation in nature. From ritzy retreats to low-cost properties and cottages that have amenities like laundry facilities, Expedia has something for all traveler tastes. As for awesome deals? We’ve got you covered!
How can I find cheap cottages in Chester?
The easiest way to compare cheap cottages in Chester is with Expedia’s filter tool. Fine-tune your search results by amenities, star rating and budget to take advantage of awesome bargains with only a few clicks.